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Chiral determination of nornicotine, anatabine and anabasine in tobacco by achiral gas chromatography with (1S)-(-)-camphanic chloride derivatization: Application to enantiomeric profiling of cultivars and curing processes.
Journal of Chromatography A ( IF 4.1 ) Pub Date : 2020-06-20 , DOI: 10.1016/j.chroma.2020.461361
Kai Cai 1 , Huina Zhao 2 , Runsheng Yin 3 , Yechun Lin 2 , Bo Lei 2 , Anping Wang 4 , Wenjie Pan 2 , Bin Cai 5 , Weichang Gao 2 , Feng Wang 2
Affiliation  

The alkaloid enantiomers are well-known to have different physiological and pharmacological effects, and to play an important role in enantioselectivity metabolism with enzymes catalysis in tobacco plants. Here, we developed an improved method for simultaneous and high-precision determination of the individual enantiomers of nornicotine, anatabine and anabasine in four tobacco matrices, based on an achiral gas chromatography-nitrogen phosphorus detector (GCNPD) with commonly available Rtx-200 column using (1S)-(-)-camphanic chloride derivatization. The method development consists of the optimization of extraction and derivatization, screening of achiral column, analysis of the fragmentation mechanisms and evaluation of matrix effect (ME). Under the optimized experimental conditions, the current method exhibited excellent detection capability for the alkaloid enantiomers, with coefficients of determination (R2) > 0.9989 and normality test of residuals P > 0.05 in linear regression parameters. The ME can be neglected for the camphanic derivatives. The limit of detection (LOD) and limit of quantitation (LOQ) ranged from 0.087 to 0.24 μg g  1 and 0.29 to 0.81 μg g  1, respectively. The recoveries and within-laboratory relative standard deviations (RSDR) were 94.3%~104.2% and 0.51%~3.89%, respectively. The developed method was successfully applied to determine the enantiomeric profiling of cultivars and curing processes. Tobacco cultivars had a significant impact on the nornicotine, anatabine, anabasine concentration and enantiomeric fraction (EF) of (R)-nornicotine, whereas the only significant change induced by the curing processes was an increase in the EF of (R)-anabasine.



中文翻译:

非手性气相色谱-(1S)-(-)-樟脑氯衍生物的非手性气相色谱法手性测定烟草中的去甲烟碱,阿那他滨和烟碱:在品种的对映体分析和固化过程中的应用。

众所周知,生物碱对映体具有不同的生理和药理作用,并且在烟草植物中通过酶催化的对映选择性代谢中起重要作用。在这里,我们开发了一种改进的方法,该方法基于非手性气相色谱-氮磷检测器(GC NPD)和常用的Rtx-200色谱柱,可以同时,高精度地测定四种烟草基质中去甲烟碱,阿那他滨和Anabasine的各个对映体使用(1S)-(-)-樟脑氯化物衍生化。方法的发展包括优化提取和衍生化,非手性色谱柱的筛选,分析碎裂机理和评估基质效应(ME)。在优化的实验条件下,目前的方法对生物碱对映异构体具有优异的检测能力,线性回归参数的测定系数(R 2)> 0.9989,残基的正态性检验P > 0.05。樟脑衍生物可以忽略ME。检测限(LOD)和定量限(LOQ)介于0.087至0.24μgg  -  1和0.29至0.81μgg  -  1, 分别。回收率和实验室内相对标准偏差(RSD R)分别为94.3%〜104.2%和0.51%〜3.89%。所开发的方法已成功地用于确定品种的对映体图谱和固化过程。烟草品种对(R)-去甲烟碱的去甲烟碱,阿那他滨,鸟嘌呤浓度和对映体分数(EF)有显着影响,而烘烤过程引起的唯一显着变化是(R)-天麻碱的EF增加。

更新日期:2020-06-24
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